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[ CAS No. 24615-84-7 ] {[proInfo.proName]}

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Product Details of [ 24615-84-7 ]

CAS No. :24615-84-7 MDL No. :MFCD00040709
Formula : C6H8O4 Boiling Point : -
Linear Structure Formula :- InChI Key :CYUZOYPRAQASLN-UHFFFAOYSA-N
M.W :144.13 Pubchem ID :90558
Synonyms :

Safety of [ 24615-84-7 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P264-P272-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P333+P313-P363-P405-P501 UN#:3265
Hazard Statements:H314-H317 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 24615-84-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 24615-84-7 ]

[ 24615-84-7 ] Synthesis Path-Downstream   1~35

  • 2
  • [ 24615-84-7 ]
  • 3-propionyloxy-propionic acid [ No CAS ]
  • 3
  • [ 24615-84-7 ]
  • [ 79-10-7 ]
YieldReaction ConditionsOperation in experiment
at 135℃; for 18h;Pyrolysis;Product distribution / selectivity; Example 1; [35] Acrylic acid-containing gas obtained by partial oxidation of propylene was subjected to a processing comprising an absorption, azeotropic separation and pu- rification steps to provide the mixture containing acrylic acid, acrylic acid dimmer and impurities with high boiling point. The acrylic acid-containing mixture was introduced to an acrylic acid recovering device equipped with a thin film evaporator having an electric heating area of 3.5 m2 at a flow rate of 250 kg per hour. The wall surface of the acrylic acid recovering device was maintained at a temperature of 150 C and operated under a pressure of 75 mmHg. Acrylic acid was recovered from the top of the device at a rate of 175 kg per hour. The pyrolysis tank disposed at the lower part of the device was operated at a temperature of 135 C and pyrolysis was performed in a retention time of 18 hours. Additionally, the bottom liquid was recycled to the top of the device at a flow rate of 870 kg per hour. The recycled liquid is about 350 wt% based on the weight of the acrylic acid-containing mixture that contains acrylic acid dimer, introduced to the acrylic acid recovering device. The remaining liquid was discarded to treat as waste oil. The composition of acrylic acid, acrylic acid dimer and other impurities with high boiling point in each stream is as follows. Acrylic Acrylic acid Other impurities with acid dimer high boiling point Stream introduced into 51.81 15.57 32.62 device Stream recovered from 83.95 1.03 15.02 top of device Waste liquid 4.7 25.3 70.0 (expressed in wt%) [36] After operation for 4 months under the above conditions, the device could be operated in a stable manner without a significant change in concentration of acrylic acid or acrylic acid dimmer in the waste liquid. Further, there was no trouble caused by polymerization or the like.; [37] Example 2; [38] Example 1 was repeated, except that a tray distillation column whose theoretical plate number is 5 was added to the top of the recovering device as shown in FIG. 2 and that acrylic acid-containing mixture was introduced to the distillation column, in order to reduce the concentration of acrylic acid dimer and impurities with high boiling point in the stream recovered from the top of the acrylic acid recovering device according to the present invention and then recycled to the preceding purification stage for removing impurities with high boiling point. The wall temperature of the thin film evaporator was controlled so that the bottom temperature of the distillation column is 90 C, and the distillation column was operated at a reflux ratio of 0.7. As a result, the composition of the stream recycled to the preceding separation column was 99.8 wt% of acrylic acid, 0.06 wt% of dimer and the balance amount of impurities.
  • 6
  • [ 24615-84-7 ]
  • polymer; monomer(s): 2-carboxyethyl acrylate [ No CAS ]
  • 7
  • [ 128454-44-4 ]
  • [ 24615-84-7 ]
  • [ 869583-47-1 ]
YieldReaction ConditionsOperation in experiment
In water; acetone; EXAMPLE 9 Preparation of 3-azido-3-oxopropyl acrylate (CEA-N3) CEA-Cl from Example 7 (109.2 g; 0.671 mole) was dissolved in acetone (135 mL). Sodium azide (57.2 g; 0.806 mole) was dissolved in water (135 mL) and chilled. The CEA-Cl solution was then added to the chilled azide solution with vigorous stirring in an ice bath for 1.5 hours. The reaction mixture was extracted two times with 150 mL of CHCl3 each extraction. The CHCl3 solution was passed through a silica gel column 40 mm in diameter by 127 mm. The 3-azido-3-oxopropyl acrylate (Compound 8) solution was gently agitated over dried molecular sieves at 4 C. overnight. The dried solution was used in Example 10 without purification.
  • 9
  • methyl β-acryloxypropionate [ No CAS ]
  • [ 6149-41-3 ]
  • [ 2544-06-1 ]
  • [ 3852-09-3 ]
  • [ 24615-84-7 ]
  • [ 503-66-2 ]
  • [ 67-56-1 ]
  • [ 292638-85-8 ]
  • [ 79-10-7 ]
YieldReaction ConditionsOperation in experiment
at 200℃; under 975.098 Torr;Product distribution / selectivity; A decomposition reaction was carried out in accordance with the present invention by using as raw material a bottom liquid of a high boiling fraction separation column in a process for producing methyl acrylate, having the following composition: [] Composition of the bottom liquid As a reactor portion at the bottom of the decomposition reaction distillation column, a stirring tank made of Hastelloy C having an internal diameter of 1000 mm and a height of 2000 mm, and a heat medium was supplied to an external jacket to control the reaction temperature at 200C, and the reaction pressure was maintained at 130 kPa. Further, at the upper portion of this stirring tank reactor, a distillation column having an internal diameter of 400 mm and a height of 4000 mm and further a condenser, were connected, whereby a decomposition reaction was carried out by a reactive distillation system. In the interior of the distillation column, as shown in Fig. 7, disk-shaped trays 2A having a diameter D1 of 280 mm were installed in five stages with a distance of 600 mm from the uppermost portion to the lowermost portion, and in-between thereof, doughnut-shaped trays 2B with an opening having an inner diameter D2 of 260 mm were installed in four stages with an equal distance. The feeding position of the raw material liquid was above the uppermost stage disk, and the above-mentioned bottom liquid as the raw material was supplied at a rate of 150 kg/hr. The liquid retention time was controlled by the liquid level in the decomposition reactor, and adjusted so that the retention time based on the discharged liquid would be 10 hours. The operation was continued for 1 month at a decomposition reaction temperature of 200C, whereby no increase of the differential pressure was observed, and it was possible to carry out the operation under a stabilized condition. After the operation, the interior of the distillation column was visually observed, whereby no accumulation of a solid substance was observed. The discharge amount of the decomposition residue during this period was 76 kg/hr on average, and the composition was analyzed by gas chromatography, and the results were as follows. [] Composition of the residue; COMPARATIVE EXAMPLE c1 A decomposition reaction was carried out for 1 month by using the same apparatus, raw material and reaction conditions as in Example c1 except that as the distillation column portion, a distillation column packed with 2000 mm of a coil pack as a packing material instead of the disk-and-doughnut type trays, was used. There was no distinct difference from Example c1 with respect to the discharge amount or the composition of the residue, but during this period, the pressure difference between the top and the bottom of the distillation column gradually increased, and upon expiration of 1 month, an increase of differential pressure of 2.6 kPa was observed. Further, after 1 month, the operation was stopped, and the packing material was taken out and visually inspected, whereby a substantial amount of a solid substance was found to have deposited. As is evident from the results of the above Examples and Comparative Examples, when the process of the present invention is employed, it is possible to carry out a continuous operation in a stabilized condition without a trouble of e.g. clogging or an increase in the differential pressure and to prevent deposition or accumulation of the solid substance.
  • 10
  • [ 92-84-2 ]
  • [ 24615-84-7 ]
  • [ 110-16-7 ]
  • [ 123-31-9 ]
  • [ 79-10-7 ]
YieldReaction ConditionsOperation in experiment
at 190℃; under 540.054 Torr;Product distribution / selectivity; Using the same apparatus (Fig. 1) as in Example a1, a high boiling material having the following composition was continuously supplied from the line 1 at a rate of 580 kg/hr. High boiling (raw material) composition A decomposition reaction was carried out under a reaction pressure of 72 kPa at a decomposition temperature of 190C for a retention of 1 hours. From the line 6 at the top, a valuable substance composed mainly of acrylic acid was recovered at a rate of 449 kg/hr, while a reaction residue having the following composition was withdrawn out of the system via the line 4 at a rate of 131 kg/hr. Composition of reaction residue The bottom liquid of the decomposition reaction column was withdrawn from a 3/4B nozzle (line 2) installed at the lowest position of the bottom portion and supplied to the pump B. Via the pump B, it was withdrawn from the line 4 at a rate of 131 kg/hr, while to the line 3, it was supplied at a rate of 32000 kg/hr as a return liquid to the decomposition reaction column via the heat exchanger C for heating by a pipe having a diameter of 4B. On the other hand, the bottom liquid of the decomposition reaction column was supplied as a return liquid by the pump B from the line 5 to form the flow in a circumferential direction in the decomposition reaction column. The pipe diameter of the line 5 was 11/2(1.5)B, and the flow rate was 400 kg/hr, and the such a control was carried out by a flow rate control valve (not shown in Fig.) installed on the line 5. After carrying out a continuous operation for 6 months, the operation was stopped, and the interior of the decomposition reaction column was inspected. No accumulation was observed at the bottom of the decomposition reaction column. Further, during the operation, no clogging was observed in the transport pipe of the reaction residue.; EXAMPLES b5 to b8 Using the same apparatus as in Example b1, a decomposition reaction was carried out by supplying a high boiling material having the following composition as the raw material at a rate of 580 kg/hr. Composition of high boiling material (raw material) The conditions of the decomposition reaction were a reaction pressure of 72 kPa, a decomposition temperature of 190C and a retention time of 1 hour, and no decomposition catalyst was supplied. From the column top, a valuable substance composed mainly of acrylic acid was recovered at a rate of 449.5 kg/hr, while from the bottom, a reaction residue having the following composition was intermittently discharged at a rate of 130.5 kg/hr. Namely, the closing time and the opening time of the intermittent discharge control valve D as shown in Fig. 6, were set as shown in Table 2, and the operation was carried out. The discharged liquid was sent to the reaction residue storage tank installed in a distance of 800 m by means of a pipe having a diameter of 3/4B (inner diameter: 22.2 mm). A continuous operation was carried out for 3 months, whereby no clogging was observed in the transport pipe for the reaction residue. Further, the decomposition ratio of the acrylic acid dimer was about 72%. The results are shown in Table 2. [] Composition of the reaction residue;EXAMPLE d2 Decomposition of a high boiling liquid was carried out by using the same apparatus as in Example d1. The composition of the high boiling liquid was 5.3 wt% of acrylic acid, 10 wt% of maleic acid, 42.4 wt% of an acrylic acid dimer (acryloxypropionic acid), 1.3 wt% of hydroquinone and 1 wt% of phenothiazine, and the liquid was supplied at a rate of 580 kg/hr. The decomposition reaction was carried out under a reaction pressure of 72 kPa at a decomposition temperature of 190C for a retention time of 1 hour, whereby a decomposition gas comprising 85.1 wt% of acrylic acid, 8.7 wt% of maleic acid, 2.1 wt% of an acrylic acid dimer (acryloxypropionic acid), 0.03 wt% of hydroquinone and 4.07 wt% of others was obtained from the top of the decomposition reaction column at a rate of 449.5 kg/hr. To the heat exchanger for cooling the decomposition gas, the liquid obtained by cooling the decomposition gas was returned at a rate of 500 kg/hr. As oxygen or the like, air was supplied at a rate of 2 Nm3/hr to the column top gas line 44a as shown in Fig. 11. After carrying out a continuous operation for 3 months, the operation was stopped, and the interior of the decomposition reaction column was inspected. No polymer was observed in the interior of the decomposition reaction column or in the heat exchanger for cooling the column top gas.
  • 11
  • [ 92-84-2 ]
  • [ 79-10-7 ]
  • [ 24615-84-7 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 9 Preparation of 3-(acryloyloxy)propanoic Acid (2-carboxyethyl Acryate; CEA) Acrylic acid (100 g; 1.39 mole) and phenothiazine (0.1 g) were placed in a 500 mL round bottom flask. The reaction was stirred at 92 C. for 14 hours. The excess acrylic acid was removed on a rotary evaporator at 25 C. using a mechanical vacuum pump. The amount of residue obtained was 51.3 g. The CEA (Compound 6) was used in Example 10 without purification.
EXAMPLE 7 Preparation of 3-(acryloyloxy)propanoic acid (2-carboxyethyl acrylate; CEA) Acrylic acid (100 g; 1.39 mole) and phenothiazine (0.1 g) were placed in a 500 mL round bottom flask. The reaction was stirred at 92 C. for 14 hours. The excess acrylic acid was removed on a rotary evaporator at 25 C. using a mechanical vacuum pump. The amount of residue obtained was 51.3 g. The CEA (Compound 6) was used in Example 7 without purification.
EXAMPLE 9 Preparation of 3-(acryloyloxy)propanoic acid (2-carboxyethyl acrylate; CEA) Acrylic acid (100 g; 1.39 mole) and phenothiazine (0.1 g) were placed in a 500 mL round bottom flask. The reaction was stirred at 92 C. for 14 hours. The excess acrylic acid was removed on a rotary evaporator at 25 C. using a mechanical vacuum pump. The amount of residue obtained was 51.3 g. The CEA (Compound 6) was used in Example 10 without purification.
  • 12
  • [ 24615-84-7 ]
  • [ 128454-44-4 ]
  • 3-chloro-3-oxopropyl 3-chloropropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
61%; 26% With oxalyl dichloride; 10H-phenothiazine; 9,10-phenanthrenequinone; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; under 200 Torr; CEA from Example 7 (51 g; ~ 0.35 mole) and dimethyl formamide (DMF; 0.2 mL; 0.26 mmole) were dissolved in CH2Cl3 (100 mL). The CEA solution was added slowly (over 2 hours) to a stirred solution of oxalyl chloride (53 mL; 0.61 <n="50"/>mole), DMF (0.2 mL; 2.6 mmole), anthraquinone (0.5 g; 2.4 mmole), phenothiazine (0.1 g, 0.5 mmole), and CH2Cl3 (75 mL) in a 500 mL round bottom flask in an ice bath at 200 mm pressure. A dry ice condenser was used to retain the CH2Cl3 in the reaction flask. After the addition was complete the reaction was stirred at room temperature overnight. The weight of reaction solution was 369 g. A sample of the CEA-Cl (Compound 7) reaction solution (124 mg) was treated with 1,4- dibromobenzene (DBB, 6.85 mg) evaporated and dissolved in CDCl3: 1H NMR (CDCl3, 400 MHz) δ 7.38 (s, 4H; DBB internal std.), 6.45 (d, IH, J = 17.4 Hz), 6.13 (dd, IH, J = 17.4, 10.4 Hz), 5.90 (d, IH, J = 10.4 Hz), 4.47 (t, 2H, J = 5.9 Hz), 3.28 (t, 2H, J = 5.9). The spectra was consistent with the desired product. There was 0.394 mole DBB for 1.0 mole CEA-Cl by integration, which gave a calculated yield of 61%. Commercially available CEA (426 g; Aldrich) was reacted with oxalyl chloride (532 mL) in a procedure similar to the one listed above. The residue CEA- Cl (490 g) was distilled using an oil bath at 1400C at a pressure of 18 mm Hg. The distillate temperature reached 980C and 150 g of distillate was collected. The distillate was redistilled at 18 mm Hg at a maximum bath temperature of 1200C. The temperature range for the distillate was 300C to 700C which gave 1 1 g of material. The distillate appeared to be 3-chloro-3-oxopropyl 3-chloropropanoate. The residue of the second distillation (125 g; 26 % of theory) was used in Example 9.
  • 13
  • [ 79-10-7 ]
  • [ 24615-84-7 ]
YieldReaction ConditionsOperation in experiment
2.37% at 0℃; for 0.166667h; The 1000 ml acrylic acid placed in an ultrasonic generator, an open circulation cooling water, regulating the cooling water temperature is 0 C, open the ultrasonic generator, power 1000W, adjustable ultrasonic frequency 100KHz, setting the ultrasonic application time is 10 minutes, begin to ultrasonic treatment.The resulting acrylic acid as colorless transparent liquid. Raw materials through Agilent1100Series detecting acrylic acid content of the high performance liquid chromatograph 85.89%, the dimer content acrylic acid 13.64% ; after being processed through the Agilent1100Series detecting acrylic acid content of the high performance liquid chromatograph 95.81%, the dimer content of 2.37%.
With 10H-phenothiazine; at 92℃; for 14h; EXAMPLE 7 Preparation of 3-(acryloyloxy)propanoic acid (2-carboxyethyl acrylate; CEA) Acrylic acid (100 g; 1.39 mole) and phenothiazine (0.1 g) were placed in a 500 mL round bottom flask. The reaction was stirred at 92 C. for 14 hours. The excess acrylic acid was removed on a rotary evaporator at 25 C. using a mechanical vacuum pump. The amount of residue obtained was 51.3 g. The CEA (Compound 6) was used in Example 7 without purification.
With 10H-phenothiazine; at 92℃; for 14h;Neat (no solvent); Acrylic acid (100 g; 1.39 mole) and phenothiazine (0.1 g) were placed in a 500 mL round bottom flask. The reaction was stirred at 920C for 14 hours. The excess acrylic acid was removed on a rotary evaporator at 250C using a mechanical vacuum pump. The amount of residue obtained was 51.3 g. The CEA (Compound 6) was used in Example 7 without purification.
With hydroquinone; In neat (no solvent); at 120 - 130℃; for 10h; FIG. 3 shows the mass spectrum for the GC peak 15.2 minutes as well as the mass spectrum for pure diacrylic acid that was generated by heating liquid acrylic acid monomer in air with 1 OOOppm hydroquinone at 120-130C for 10 hours (after the 10 hours, GC-MS analysis of the liquid showed it to be composed of approximately 25% acrylic acid monomer and 75% diacrylic acid). The most prominent mass spectral peaks for the diacrylic acid were found at 45, 55, 73 and 89 m/z which corresponded to the mass fragments COOH+, CH2=CHCO+, CH2CH2COOH+ and OCH2CH2COOH+. The molecular weight of the diacrylic acid was calculated to be 144 amu and a mass ion at 145 m/z was detected in the mass spectrum for this compound which could correspond to the protonated diacrylic acid molecule.

  • 14
  • [ 24615-84-7 ]
  • [ 128454-44-4 ]
YieldReaction ConditionsOperation in experiment
26% With oxalyl dichloride; 10H-phenothiazine; 9,10-phenanthrenequinone; In N,N-dimethyl-formamide; at 0 - 20℃; under 200 Torr;Product distribution / selectivity; EXAMPLE 8Preparation of 3-chloro-3-oxopropyl acrylate (CEA-Cl)CEA from Example 7 (51 g; 0.35 mole) and dimethyl formamide (DMF; 0.2 mL; 0.26 mmole) were dissolved in CH2Cl3 (100 mL). The CEA solution was added slowly (over 2 hours) to a stirred solution of oxalyl chloride (53 mL; 0.61 mole), DMF (0.2 mL; 2.6 mmole), anthraquinone (0.5 g; 2.4 mmole), phenothiazine (0.1 g, 0.5 mmole), and CH2Cl3 (75 mL) in a 500 mL round bottom flask in an ice bath at 200 mm pressure. A dry ice condenser was used to retain the CH2Cl3 in the reaction flask. After the addition was complete the reaction was stirred at room temperature overnight. The weight of reaction solution was 369 g. A sample of the CEA-Cl (Compound 7) reaction solution (124 mg) was treated with 1,4-dibromobenzene (DBB, 6.85 mg) evaporated and dissolved in CDCl3: 1H NMR (CDCl3, 400 MHz) δ 7.38 (s, 4H; DBB internal std.), 6.45 (d, 1H, J=17.4 Hz), 6.13 (dd, 1H, J=17.4, 10.4 Hz), 5.90 (d, 1H, J=10.4 Hz), 4.47 (t, 2H, J=5.9 Hz), 3.28 (t, 2H, J=5.9). The spectra was consistent with the desired product. There was 0.394 mole DBB for 1.0 mole CEA-Cl by integration, which gave a calculated yield of 61%. Commercially available CEA (426 g; Aldrich) was reacted with oxalyl chloride (532 mL) in a procedure similar to the one listed above. The residue CEA-Cl (490 g) was distilled using an oil bath at 140 C. at a pressure of 18 mm Hg. The distillate temperature reached 98 C. and 150 g of distillate was collected. The distillate was redistilled at 18 mm Hg at a maximum bath temperature of 120 C. The temperature range for the distillate was 30 C. to 70 C. which gave 11 g of material. The distillate appeared to be 3-chloro-3-oxopropyl 3-chloropropanoate. The residue of the second distillation (125 g; 26% of theory) was used in Example 9.
With thionyl chloride; at 0 - 17℃; for 4.5h; To the pale yellow oil containing bisphenol was added 28 g of a 50% aqueous potassium hydroxide solution, a temperature of the solution was raised to 98 C., and the solution was retained at the same temperature for 3 hours. Thereafter, the solution was cooled to 50 C., hexane was added, and this was dehydrated under warming to a liquid temperature of 106 C., and cooled to 3 C. (this solution is designated A solution).Another container was charged with 35.3 g of <strong>[24615-84-7]2-carboxyethyl acrylate</strong>, and this was cooled to 1 C. under stirring. To this was added dropwise 26.7 g of thionyl chloride over 1.5 hours while retaining at 0 to 1 C. Thereafter, a temperature was retained at 1 to 17 C. for 3 hours, followed by degassing for 3 hours under reduced pressure (this solution is designated B solution).To the A solution was added dropwise the B solution over 1 hour while retaining at 1 to 3 C., and a temperature was retained at the same temperature for 30 minutes. To this was added 150 ml of water, this was washed with water at 10 to 30 C., and the oily layer was obtained by layers separation. According to the same procedure, washing with water was repeated a total of three times. Thereby, 303 g of the brown oily layer was obtained.When the resulting oily layer was analyzed by liquid chromatography, it was found out that 6.3% by weight of a compound represented by the formula (1-1)(hereinafter, referred to as Compound (1-1) in some cases) was contained in the composition except for the solvent. From the resulting oily layer, Compound (1-1) was isolated by a large scale collecting system (8A Type, manufactured by Shimadzu Corporation) using Sumipax ODS A-210 (diameter 20 mm×height 25 cm, diameter of filler: 5 μm) as a column.Compound (1-1) was measured for 1H NMR spectrum using ECA-500 manufactured by JEOL and employing tetramethylsilane as an internal standard. 1H NMR(500.16 MHz, CDCl3) δ (ppm):0.49(3H, (a)), 0.55(3H, (b)), 0.66(3H,(c)), 0.70(3H,(d)), 1.01(3H,(e)), 1.03 (3H,(f)), 1.19-1.38(23H,(g)-(l)), 1.48(3H,(m)), 1.57-1.99(7H,(n)-(p)), 3.09(2H,(q)), 3.89(1H,(r)), 4.61-4.64(2H,(s)), 5.55(1H,(t)), 5.72(1H, (u)), 6.04(1H, (v)), 6.36(1H, (w)), 6.49(1H, (x)), 7.12(3H,(y))
  • 15
  • [ 79-10-7 ]
  • [ 24615-84-7 ]
  • polyacrylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 10H-phenothiazine; 4-methoxy-phenol; at 104.9 - 107.3℃;Product distribution / selectivity; The product gas mixture (177 184 kg/h) is cooled in a spray cooler (quench 1) operated in cocurrent by direct cooling to a temperature of 107.3 C.The liquid to be used for the direct cooling of the product gas mixture (quench liquid 1) is a portion of a mixture 1 of bottoms liquid which is withdrawn from the bottom of the condensation column described below, and a small amount (251 kg/h) of condensate withdrawn from the quench circuit 0.Contents of this mixture 1 (temperature=104.9 C.) are:
  • 16
  • [ 1026274-28-1 ]
  • [ 24615-84-7 ]
  • acrylic acid 2-{3-[2-chloro-4-(2,4-difluoro-phenylamino)-benzoyl]-4-methyl-phenylcarbamoyl}-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
2-Carboxyethyl acrylate (0.041 mL, 0.35 MMOL) was dissolved in dry DMF (7 mL). HATU (0.13 g, 0.35 MMOL) was added followed by addition of 2,4, 6-trimethylpyridine (0.07 mL, 0.54 MMOL). The mixture was stirred for 0.5 h after which compound 494 (0.10 g, 0.27 MMOL) was added. The mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated in vacuo and the crude product was purified by flash chromatography using a gradient of EtOAc/petroleum ether (40-60) 15: 85-> 70: 30 as the eluent. This afforded the title compound as oil. 13C NMR (DMSO-d6) 8 196.1, 168.3, 166.1, 159. 2 (dd), 155.6 (dd), 148. 2,139. 6,135. 4,135. 1,133. 8, 133.5, 131.8, 131.4, 128.6, 128.0, 124.6 (dd), 124.3 (dd), 122.6, 120.7, 116.2, 112.6, 111.6 (dd), 104.9 (dd), 60.4, 36.6, 19.7
  • 17
  • polyacrylic acid resin [ No CAS ]
  • [ 71-36-3 ]
  • [ 141-32-2 ]
  • [ 24615-84-7 ]
  • [ 79-10-7 ]
  • 18
  • polyacrylic acid resin [ No CAS ]
  • [ 24615-84-7 ]
  • [ 79-10-7 ]
  • 19
  • polyacrylic acid resin [ No CAS ]
  • [ 24615-84-7 ]
  • [ 7732-18-5 ]
  • [ 79-10-7 ]
  • 20
  • [ 79-10-7 ]
  • acrylic acid homopolymers [ No CAS ]
  • [ 24615-84-7 ]
YieldReaction ConditionsOperation in experiment
With 10H-phenothiazine; hydroquinone; In water; acetic acid; toluene; for 16h;Heating / reflux;Conversion of starting material; Example 1 (Comparative); (Multi-Component Inhibitor System Comprised Hydroquinone and Phenothiazine, without a Reduced Halide-Content Azine Dye-Based Compound) An aqueous acrylic acid product stream was purified (i.e., dehydrated) by azeotropic distillation in the aforesaid distillation column tinder the following conditions: 215 mm Hg top pressure 294 g/hr aqueous AA feed rate 490 g/hr toluene reflux rate 92 C. control tray temperature Aqueous acrylic acid was fed to the distillation column at tray 20 and toluene reflux was fed to the top tray at the rate indicated. The aqueous acrylic acid feed stream composition contained 73.6 wt % acrylic acid, 0.8 wt % beta-acryloxypropionic acid (AOPA), 21.9 wt % water, 3.1 wt % acetic acid, and 0.6 wt % other minor components such as formaldehyde, formic acid, maleic acid, and hydroquinone polymerization inhibitor. An inhibitor solution of 1.0 wt % phenothiazine and 1.31 wt % hydroquinone in glacial acrylic acid was fed into the distillation column at trays 15 and 24, each at a rate of 9.9 g/hr. An additional stream of 1.0 wt % phenothiazine and 2.0 wt % hydroquinone in glacial acrylic acid was fed to the top tray at a rate of 0.7 g/hr. The inhibitor feeds resulted in inhibitor levels in the bottoms of approximately 900 ppm phenothiazine and 1500 ppm hydroquinone. Bottoms product was collected at a rate of 240 g/hr and contained 94.8 wt % acrylic acid, 3.7 wt % beta-acryloxypropionic acid, 5760 ppm acetic acid, and <10 ppm toluene. Aqueous distillate was collected at a rate of 74 g/hr and contained 83.0% water, 2.6 wt % acrylic acid, and 14.4 wt % acetic acid. The column was operated for two eight-hour runs. The amount of polymer deposited in the column at the end of each eight hour run was estimated by visual inspection. Each tray section was examined for size and distribution of polymer. The polymer was rated on a scale from 1 to 5 for size, ranging from 0.7 mm diameter (a rating of 1.0) to 2.8 mm diameter (a rating of 5). The polymer was also rated on a scale of 1 to 5 for distribution, where the numbers indicate the number of particles of the same size. The product of these ratings in each tray section were summed over the entire column to give a total column polymer count. After eight hours on stream the total column polymer count was about 30, and after sixteen hours it was about 31.
With 10H-phenothiazine; methylene blue; hydroquinone; In water; acetic acid; toluene; for 16h;Heating / reflux;Conversion of starting material; Example 2 (Comparative); (Multi-Component Inhibitor System Comprised Methylene Blue, Hydroquinone, and Phenothiazine) Methylene blue is a thiazine dye-based compound, but is not of reduced halide-content. An aqueous acrylic acid product stream was purified (i.e., dehydrated) by azeotropic distillation in the aforesaid distillation column under the following conditions: 215 mm Hg top pressure 287 g/hr aqueous AA feed rate 553 g/hr toluene reflux rate 92 C. control tray temperature Aqueous acrylic acid was fed to the distillation column at tray 20 and toluene reflux was fed to the top tray at the rate indicated. The aqueous acrylic acid feed stream composition contained 64.0 wt % acrylic acid, 0.5 wt % beta-acryloxypropionic acid (AOPA), 32.3 wt % water, 2.5 wt % acetic acid, and 0.7 wt % other minor components such as formaldehyde, formic acid, maleic acid, and hydroquinone polymerization inhibitor, based on the total weight of the feed stream. An inhibitor solution of 1.0 wt % phenothiazine and 1.17 wt % hydroquinone in glacial acrylic acid was fed into the distillation colurnn at trays 15 and 24, each at a rate of 9.9 g/hr. An additional stream of 1.0 wt % phenothiazine and 2.0 wt % hydroquinone in glacial acrylic acid was fed to the top tray at a rate of 0.7 g/hr. A solution of 0.44 wt % tetramethylthionine chloride in water was fed to tray 18. The inhibitor feeds resulted in iinibitor levels in the bottoms of approximately 900 ppm phenothiazine, 1500 ppm hydroquinone and 100 ppm tetramethylthionine chloride. Bottoms product was collected at a rate of 213 g/hr and contained 95.3 wt % acrylic acid, 3.0 wt % beta-acryloxypropionic acid, 3400 ppm acetic acid, and <10 ppm toluene. Aqueous distillate was collected at a rate of 99 g/hr and contained 85.8% water, 2.3 wt % acrylic acid, and 11.9 wt % acetic acid. The column was operated for two eight-hour runs. After eight hours on stream the total column polymer count resulting from this Example 2 was about 18, and after 16 hours it was about 12. Example 6; (Comparative) (Multi-Component Inhibitor System Comprised Methylene Blue, Hydroquinone, and Phenothiazine) The azeotropic distillation of comparative Example 2 was repeated with a higher concentration of tetramethylthionine chloride. The aqueous acrylic acid was fed at 287 g/hr and its composition contained 65.8 wt % acrylic acid, 0.4 wt % beta-acryloxypropionic acid (AOPA), 29.7 wt % water, 2.6 wt % acetic. acid, and 1.5 wt % other minor components such as formaldehyde, formic acid, maleic acid, and hydroquinone polymerization inhibitor. The toluene reflux was fed to the top tray at a rate of 459 g/hr. An inhibitor solution of 1.0 wt % phenothiazine and 1.17 wt % hydroquinone in glacial acrylic acid was fed into the distillation column at trays 15 and 24, each at a rate of 9.9 g/hr. An additional stream of 1.0 wt % phenothiazine and 2.0 wt % hydroquinone in glacial acrylic acid was fed to the top tray at a rate of 0.7 g/hr. A solution of 1.32 wt % tetramethylthionine chloride in water was fed to tray 18. The inhibitor feeds resulted in inhibitor levels in the bottoms of approximately 900 ppm phenothiazine, 1500 ppm hydroquinone and 296 ppm tetramethylthionine chloride. Bottoms product was collected at a rate of 216 g/hr and contained 96.6 wt % acrylic acid, 3.0 wt % beta-acryloxypropionic acid, 3650 ppm acetic acid, and <10 ppm toluene. Aqueous distillate was collected at a rate of 96 g/hr and contained 82.6% water, 2.2 wt % acrylic acid, and 15.2 wt % acetic acid. The column was operated for two eight-hour runs. After eight hours on stream the total column polymer count was about 88, and after sixteen hours it was about 40.
With tetramethylthionine sulfate; 10H-phenothiazine; hydroquinone; In water; acetic acid; toluene; for 16h;Heating / reflux;Conversion of starting material; Example 3; (Multi-Component Inhibitor System Comprised Tetramethylthionine Sulfate, Hydroquinone, and Phenothiazine) The azeotropic distillation of comparative Example 2 was repeated with the substitution of tetramethylthionine sulfate for tetramethylthionine chloride. Tetramethylthionine sulfate is a reduced halide-content azine dye-based compound of the thiazine dye family of compounds. The aqueous acrylic acid product stream was fed at 293 g/hr and its composition contained 69.1 wt % acrylic acid, 0.9 wt % beta-acryloxypropionic acid (AOPA), 25.2 wt % water, 3.1 wt % acetic acid, and 1.7 wt % other minor components such as formaldebyde, formic acid, maleic acid, and bydroquinolie polymerization inhibitor. The toluene reflux was fed to the top tray at a rate of 595 g/hr. An inhibitor solution of 1.0 wt % phenothiazine and 1.30 wt % hydroquinone in glacial acrylic acid was fed into the distillation column at trays 15 and 24, each at a rate of 9.9 g/hr. An additional stream of 1.0 wt % phenothiazine and 2.0 wt % hydroquinone in glacial acrylic acid was fed to the top tray at a rate of 0.7 g/hr. A solution of 0.55 wt % tetramethylthionine sulfate in water was fed to tray 18. The inhibitor feeds resulted in inhibitor levels in the bottoms of approximately 900 ppm phenothiazine, 1500 ppm hydroquinone and 135 ppm tetramethylthionine sulfate. Bottoms product was collected at a rate of 220 g/hr and contained 94.7 wt % acrylic acid, 3.02 wt % beta-acryloxypropionic acid, 4600 ppm acetic acid, and <10 ppm toluene. Aqueous distillate was collected at a rate of 99 g/hr and contained 78.8% water, 2.0 wt % acrylic acid, and 19.2 wt % acetic acid. The column was operated for two eight-hour runs. After eight hours on stream the total column polymer count was about 4, and after sixteen hours it was about 3, which is only about 23% of the polymer count achieved by the methylene blue-containing inhibitor system used in comparative Example 2. In addition, since the tetramethylthionine sulfate was a reduced halide-content compound, a reduction in equipment corrosion was expected. Example 7; (Multi-Component Inhibitor System Comprised Tetramethylthionine Sulfate, Hydroquinone, and Phenothiazine) The azeotropic distillation of comparative Example 2 was repeated with the substitution of tetramethylthionine sulfate for tetramethylthionine chloride, but at a higher concentration. The aqueous acrylic acid was fed at 293 g/hr and its composition contained 69.1 wt % acrylic acid, 0.9 wt % beta-acryloxypropionic acid (AOPA), 25.2 wt % water, 3.1 wt % acetic acid, and 1.7% other minor components such as formaldehyde, formic acid, maleic acid, and hydroquinone polymerization inhibitor. The toluene reflux was fed to the top tray at a rate of 587 g/hr. An inhibitor soluition of 1.0 wt % phenotbiazine and 1.31 wt % hydroquinone in glacial acrylic acid was fed into the distillation colum at trays 15 and 24, each at a rate of 9.9 g/hr. An additional stream of 1.0 wt % phenothiazine and 2.0 wt % hydroquinone in glacial acrylic acid was fed to the top tray at a rate of 0.7 g/hr. A solution of 1.0 wt % tetrarietltylthionine sulfate in water was fed to tray 18. The inhibitor feeds resulted in inhibitor levels in the bottoms of approximately 900 ppm phenothiazine, 1500 ppm hydroquinone and 230 ppm tetramethylthionine sulfate. Bottoms product was collected at a rate of 217 g/hr and contained 93.7 wt % acrylic acid, 3.4 wt % beta-acryloxypropionic acid, 5100 ppm acetic acid, and <10 ppm toluene. Aqueous distillate was collected at a rate of 93 g/hr and contained 78.1% water, 2.3 wt % acrylic acid, and 19.6 wt % acetic acid. The column was operated for one eight-hour run before flooding required a shutdown and, therefore, a second 8-hour run was not possible under the foregoing conditions. After eight hours on stream the total column polymer count was about 29, which is greater than comparative Example 2 and less than comparative Example 6 (which both included tetramethylthionine chloride), but more than Example 3 (which employed a lesser amount of the tetramethylthionine sulfate). Since the tetramethylthionine sulfate was of reduced halide-content, a reduction in equipment corrosion was expected.
With tetramethylthionine acetate; 10H-phenothiazine; hydroquinone; In water; acetic acid; toluene; for 16h;Heating / reflux;Conversion of starting material; Example 4; (Multi-Component Inhibitor System Comprised Tetramethylthionine Acetate, Hydroquinone, and Phenothiazine) The azeotropic distillation of comparative Example 2 was repeated with the substitution of tetramethylthionine acetate for tetramethylthionine chloride. Tetramethylthionine acetate is a reduced halide-content azine dye-based compound of the thiazine dye family of compounds. The aqueous acrylic acid was fed at 293 g/hr and its composition contained 69.8 wt % acrylic acid, 0.8 wt % beta-acryloxypropionic acid (AOPA), 24.8 wt % water, 3.0 wt % acetic acid, and 1.6 wt % other minor components such as formaldehyde, formic acid, maleic acid, and hydroquinone polymerization inhibitor. The toluene reflux was fed to the top tray at a rate of 574 g/hr. An inhibitor solution of 1.0 wt % phenothiazine and 1.31 wt % hydroquinone in glacial acrylic acid was fed into the distillation column at trays 15 and 24, each at a rate of 9.9 g/hr. An additional stream of 1.0 wt % phenothiazine and 2.0 wt % hydroquinone in glacial acrylic acid was fed to the top tray at a rate of 0.7 g/hr. A solution of 0.44 wt % tetramethylthionine acetate in water was fed to tray 18. The inhibitor feeds resulted in inhibitor levels in the bottoms of approximately 900 ppm phenothiazine, 1500 ppm hydroquinone and 100 ppm tetramethylthionine acetate. Bottoms product was collected at a rate of 215 g/hr and contained 94.5 wt % acrylic acid, 3.6 wt % beta-acryloxypropionic acid, 4100 ppm acetic acid, and <10 ppm toluene. Aqueous distillate was collected at a rate of 95 g/hr and contained 83.9% water, 2.7 wt % acrylic acid, and 13.5 wt % acetic acid. The column was operated for two eight-hour runs. After eight hours on stream the total column polymer count was about 8, and after sixteen hours it was about 36. Thus, a polymerization inhibitor which comprised tetramethylthionine acetate inhibited polymerization and, since it was of reduced halide-content, a reduction in equipment corrosion was expected. Example 8; (Multi-Component Inhibitor System Comprised Tetramethylthionine Acetate, Hydroquinone, and Phenothiazine) The azeotropic distillation of comparative Example 2 was repeated with the substitution of tetramethylthionine acetate for tetramethylthionine chloride. The aqueous acrylic acid was fed at 293 g/hr and its composition contained 75.5 wt % acrylic acid, 0.7 wt % beta-acryloxypropionic acid (AOPA), 20.3 wt % water, 3.0 wt % acetic acid, and 0.5 wt % other minor components such as formaldehyde, formic acid, maleic acid, and hydroquinone polymerization inhibitor. The toluene reflux was fed to the top tray at a rate of 466 g/hr. An inhibitor solution of 1.0 wt % phenothiazine and 1.31 wt % hydroquinone in glacial acrylic acid was fed into the distillation column at trays 15 and 24, each at a rate of 9.9 g/hr. An additional stream of 1.0 wt % phenothiazine and 2.0 wt % hydroquinone in glacial acrylic acid was fed to the top tray at a rate of 0.7 g/hr. A solution of 0.99 wt % tetramethylthionine acetate in water was fed to tray 18. The inhibitor feeds resulted in inhibitor levels in the bottoms of approximately 900 ppm phenothiazine, 1500 ppm hydroquinone and 317 ppm tetramethylthionine acetate. Bottoms product was collected at a rate of 238 g/hr and contained 91.2 wt % acrylic acid, 3.8 wt % beta-acryloxypropionic acid, 6170 ppm acetic acid, and <10 ppm toluene. Aqueous distillate was collected at a rate of 76 g/hr and contained 79.2% water, 2.2 wt % acrylic acid, and 18.6 wt % acetic acid. The column was operated for two eight-hour runs. After eight hours on stream the total column polymer count was about 18, and after sixteen hours it was about 89. Thus, a polymerization inhibitor which comprised tetramethylthionine acetate inhibited polymerization at a level comparable to comparative Example 6 and, since it was of reduced halide-content, a reduction in equipment corrosion was expected.
With tetramethylthionine phtalate; 10H-phenothiazine; hydroquinone; In water; acetic acid; toluene; for 16h;Heating / reflux;Conversion of starting material; Example 5; (Multi-Component Inhibitor System Comprised Tetramethylthionine Phthalate, Hydroquinone, and Phenothiazine) The azeotropic distillation of comparative Example 2 was repeated with the substitution of tetramethylthionine phthalate for tetramethylthionine chloride. Tetramethylthionine phthalate is a reduced halide-content azine dye-based compound of the thiazine dye family of compounds. The aqueous acrylic acid was fed at 292 g/hr and its composition contained 69.1 wt % acrylic acid, 0.9 wt % beta-acryloxypropionic acid (AOPA), 25.2 wt % water, 3.1 wt % acetic acid, and 1.7 wt % other minor components such as formaldehyde, formic acid, maleic acid, and hydroquinone polymerization inhibitor. The toluene reflux was fed to the top tray at a rate of 586 g/hr. An inhibitor solution of 1.0 wt % phenothiazine and 1.31 wt % hydroquinone in glacial acrylic acid was fed into the distillation column at trays 15 and 24, each at a rate of 9.9 g/hr. An additional stream of 1.0 wt % phenothiazine and 2.0 wt % hydroquinone in glacial acrylic acid was fed to the top tray at a rate of 0.7 g/hr. A solution of 0.77 wt % tetramethylthionine phthalate in water was fed to tray 18. The inhibitor feeds resulted in inhibitor levels in the bottoms of approximately 900 ppm phenothiazine, 1500 ppm hydroquinone and 185 ppm tetramethylthionine phthalate. Bottoms product was collected at a rate of 224 g/hr and contained 93.6 wt % acrylic acid, 3.0 wt % beta-acryloxypropionic acid, 3770 ppmr acetic acid, and <10 ppm toluene. Aqueous distillate was collected at a rate of 94 g/hr and contained 73.8% water, 2.5 wt % acrylic acid, and 23.7 wt % acetic acid. The column was operated for one eight-hour run before flooding required a shutdown and, therefore, a second 8-hour run was not possible under the foregoing conditions. After eight hours on stream the total column polymer count was about 17. Thus, a polymerization inhibitor which comprised tetramethylthionine acetate inhibited polymerization at a level comparable to comparative Example 2 and, since it was of reduced halide-content, a reduction in equipment corrosion was expected.
With 10H-phenothiazine; Nile blue A; hydroquinone; In water; acetic acid; toluene; for 16h;Heating / reflux;Conversion of starting material; Example 9; (Multi-Component Inhibitor System Comprised Nile Blue A, Hydroquinone, and Phenothiazine) The azeotropic distillation of comparative Example 2 was repeated with the substitution of 5-amino-4-(diethylamino)benzo[a]phenoxazinium hydrogen sulfate (Nile Blue A) for tetramethylthionine chloride. Nile Blue A is a reduced halide-content azine dye-based compound of the oxazine dye family of compounds. The aqueous acrylic acid was fed at 293 g/hr and its composition contained 72.6 wt % acrylic acid, 0.9 wt % beta-acryloxypropionic acid (AOPA), 21.5 wt % water, 3.2 wt % acetic acid, and 1.8 wt % other minor components such as formaldehyde, formic acid, maleic acid, and hydroquinone polymerization inhibitor. The toluene reflux was fed to the top tray at a rate of 485 g/hr. An inhibitor solution of 1.0 wt % phenothiazine and 1.31 wt % hydroquinone in glacial acrylic acid was fed into the distillation column at trays 15 and 24, each at a rate of 9.9 g/hr. An additional stream of 1.0 wt % phenothiazine and 2.0 wt % hydroquinone in glacial acrylic acid was fed to the top tray at a rate of 0.7 g/hr. A solution of 0.55 wt % Nile Blue A in water was fed to tray 18. The inhibitor feeds resulted in inhibitor levels in the bottoms of approximately 900 ppm phenothiazine, 1500 ppm hydroquinone and 125 ppm Nile Blue A. Bottoms product was collected at a rate of 238 g/hr and contained 94.0 wt % acrylic acid, 2.8 wt % beta-acryloxypropionic acid, 4800 ppm acetic acid, and <10 ppm toluene. Aqueous distillate was collected at a rate of 81 g/hr and contained 73.3% water, 2.4 wt % acrylic acid, and 24.3 wt % acetic acid. The column was operated for two eight-hour runs. After eight hours on stream the total column polymer count was about 7, and after sixteen hours it was about 14. Thus, a polymerization inhibitor which comprised Nile Blue A inhibited polymerization better than comparative Example 2 and, since it was of reduced halide-content, a reduction in equipment corrosion was expected.

  • 21
  • [ 24615-84-7 ]
  • [ 1471-17-6 ]
  • [ 79-10-7 ]
  • poly-(acrylic acid-co-3-(acryloyloxy)-propionic acid-co-pentaerythritol allyl ether) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis(isobutyronitrile); In hexane; at 55 - 60℃; for 4h;Product distribution / selectivity; Example 1; A 500-mL four-necked flask equipped with a stirrer, thermometer, nitrogen inlet tube and condenser was charged with 40 g (0.56 mole, 38.1 mL) of acrylic acid, 1.2 g of 3-(acryloyloxy)-propionic acid (trademark of Toagosei Co., Ltd.: Aronix M-5600), 0.20 g of pentaerythritol allyl ether, 0.13 g (0.00079 mole) of α,α'-azobisisobutyronitrile and 177 g (264 mL) of normalhexane, followed by uniform stirring for mixing up. Thereafter, for removing the oxygen occurring in the reaction vessel upper space, raw materials and solvent, nitrogen gas was blown into the solution. Then, while the temperature was maintained at 55 to 60 C., the reaction was allowed to proceed in a nitrogen atmosphere for 4 hours. After completion of the reaction, the slurry formed was heated to 90 C. to distill off the normalhexane, whereupon 39 g of a carboxyl group-containing water-soluble polymer was obtained as white particles with a median particle diameter of 348 μm.
With 2,2'-azobis(isobutyronitrile); In 1,2-dichloro-ethane; at 70 - 75℃; for 4h;Product distribution / selectivity; Example 4; A 500-mL four-necked flask equipped with a stirrer, thermometer, nitrogen inlet tube and condenser was charged with 40 g (0.56 mole, 38.1 mL) of acrylic acid, 1.2 g of 3-(acryloyloxy)-propionic acid (trademark of Toagosei Co., Ltd.: Aronix M-5600), 0.20 g of pentaerythritol allyl ether, 0.01 g (0.00006 mole) of α,α'-azobisisobutyronitrile and 330 g (264 mL) of ethylene dichloride, followed by uniform stirring for mixing up. Thereafter, for removing the oxygen occurring in the reaction vessel upper space, raw materials and solvent, nitrogen gas was blown into the solution. Then, while the temperature was maintained at 70 to 75 C., the reaction was allowed to proceed in a nitrogen atmosphere for 4 hours. After completion of the reaction, the fine powder-based slurry formed was heated to 105 C. to distill off the ethylene dichloride, whereupon 41 g of a carboxyl group-containing water-soluble polymer was obtained as a white fine powder. The carboxyl group-containing water-soluble polymer obtained occurred as a fine powder and the whole quantity thereof passed through a standard sieve with a mesh size of 75 μm; therefore, the median particle diameter could not be determined.
  • 22
  • [ 24615-84-7 ]
  • [ 1471-17-6 ]
  • [ 79-10-7 ]
  • poly-(acrylic acid-co-3-(acryloyloxy)-propionic acid-co-diethylene glycol diallyl ether) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis(isobutyronitrile); In hexane; at 55 - 60℃; for 4h; Example 2; A 500-mL four-necked flask equipped with a stirrer, thermometer, nitrogen inlet tube and condenser was charged with 45 g (0.625 mole, 42.9 mL) of acrylic acid, 0.9 g of 3-(acryloyloxy)-propionic acid (trademark of Toagosei Co., Ltd.: Aronix M-5600), 0.40 g of diethylene glycol diallyl ether, 0.14 g (0.00085 mole) of α,α'-azobisisobutyronitrile and 150 g (224 mL) of normalhexane, followed by uniform stirring for mixing up. Thereafter, for removing the oxygen occurring in the reaction vessel upper space, raw materials and solvent, nitrogen gas was blown into the solution. Then, while the temperature was maintained at 55 to 60 C., the reaction was allowed to proceed in a nitrogen atmosphere for 4 hours. After completion of the reaction, the slurry formed was heated to 90 C. to distill off the normalhexane, whereupon 43 g of a carboxyl group-containing water-soluble polymer was obtained as white particles with a median particle diameter of 185 μm.
  • 23
  • [ 57-57-8 ]
  • [ 367-27-1 ]
  • [ 24615-84-7 ]
  • [ 777-28-6 ]
  • 24
  • [ 57-57-8 ]
  • [ 2713-33-9 ]
  • [ 24615-84-7 ]
  • [ 926256-60-2 ]
  • 25
  • [ 79-37-8 ]
  • [ 24615-84-7 ]
  • [ 128454-44-4 ]
YieldReaction ConditionsOperation in experiment
In N-methyl-acetamide; dichloromethane; Step 1: Preparation of acrylic acid 2-chlorocarbonyl ethyl ester To a stirred 0 C. solution of acrylic acid-2-carboxyethyl ester (distilled Aldrich sample, 11.2 g, 78 mmol) in 35 mL of methylene chloride containing 3 drops of dimethylformamide was added dropwise a solution of oxalyl chloride (Alfa, 11.8 g, 93 mmol) in 10 mL of methylene chloride. When the addition was complete, the reaction flask was removed from the ice bath and the reaction mixture was allowed to warm to room temperature and was stirred overnight. The solvent and excess oxalyl chloride were then removed at reduced pressure to leave 11.6 g of the desired acid chloride as a colorless liquid. NMR and IR spectral analyses confirmed the structure of the product.
  • 26
  • [ 24615-84-7 ]
  • [ 24835-08-3 ]
  • [ 1251836-30-2 ]
YieldReaction ConditionsOperation in experiment
3-(Acryloyloxy)propionic acid (5.7 g, 40.0 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (7.6 g, 40.0 mmol) and triethylamine (5.4 g, 53.0 mmol) were added to a solution of 2-nitrobenzylamine hydrochloride (5.0 g, 26.5 mmol) in 20 ml of dichloromethane, followed by stirring at room temperature for 3 hours. After the reaction, chloroform and water were added, and the organic layer was separated, dried with saturated aqueous sodium chloride and over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was dissolved in 100 ml of ethanol, and sodium hydroxide (2.1 g, 53.0 mmol) and 50 ml of water were added, followed by stirring at room temperature for 2 hours. After the reaction, the reaction mixture was concentrated under reduced pressure and neutralized with concentrated hydrochloric acid, ethyl acetate was added, and the organic layer was separated, dried with saturated aqueous sodium chloride and over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=9/1 to 0/1) to obtain 1.53 g of the desired product.
  • 27
  • cyclohexane-1,4-dimethanole diglycidyl ether [ No CAS ]
  • [ 24615-84-7 ]
  • [ 1338828-96-8 ]
YieldReaction ConditionsOperation in experiment
73% With triethylamine; at 60℃; for 4h;Inert atmosphere; 2-Carboxyethyl acrylate (28.826 g, 0.2 mol), 1,4-cyclohexanedimethanol diglycidyl ether (25.634 g, 0.1 mol) and triethylamine (2 wt % based on 1,4-cyclohexanedimethanol diglycidyl ether) were sequentially added to a 4-bulb glass flask reactor equipped with a reflux condenser, a nitrogen inlet, a stirrer and a heater. After raising temperature to 60 C., reaction was carried out for 4 hours without using a polymerization inhibitor. Then, after cooling to room temperature and transferring to a separatory funnel, 5% HCl aqueous solution was added to neutralize the remaining catalyst and the salt was removed. Then, after washing 2 to 3 times with distilled water, a Michael acceptor having hydroxyl groups was obtained at 50 C. under reduced pressure as transparent liquid. The Michael acceptor was separated and purified to obtain a main product with the byproduct removed. FIG. 5 shows an FT-IR spectrum of the Michael acceptor prepared in Example 2. FIGS. 6, 7 and 8 respectively show a 1H-NMR spectrum, a 13C-NMR spectrum and a prep-LC result. prep-LC (yield): 73%.IR (KBr, cm-1): 3421 (-OH), 2919 (aliphatic C-H), 1727 (C═O), 1635 & 1618 (C═C), 1186 & 1122 (C-O-C), 984 (═CH2 twisting vibration). 1H-NMR (CDCl3, 300 MHz), δ (ppm): 5.80-6.33 (m, 3H, -CH═CH2), 4.32-4.40 (m, 2H, -COOCH2CH2COO-), 3.91-4.17 (m, 3H, -COOCH2CHOHCH2-), 3.22-3.57 (m, 4H, -CHOHCH2OCH2-), 2.60-2.68 (m, 2H, -CH2COO-), 0.85-2.60 (m, 5H, -CHCH2CH2CH-(cyclohexane)). 13C-NMR (CDCl3, 75 MHz), δ (ppm): 173.54 (-CH2COO-), 165.54 (CH2═CHCOO-), 130.93 (CH2═CH-), 127.54 (CH2═CH-), 68.13-74.42 (-COOCH2CHOHCH2OCH2CH-), 59.41 (CH2═CHCOOCH2-), 37.53 (cyclohexane, -CHCH2-), 33.00 (-CH2COO-), 28.72 (cyclohexane, -CHCH2CH2CH-).
  • 28
  • [ 24615-84-7 ]
  • C35H56O15 [ No CAS ]
  • 29
  • [ 24615-84-7 ]
  • C59H96N4O21 [ No CAS ]
  • 30
  • glycerol diglycidyl ether [ No CAS ]
  • [ 24615-84-7 ]
  • C32H52O17 [ No CAS ]
  • 31
  • glycerol diglycidyl ether [ No CAS ]
  • [ 24615-84-7 ]
  • [ 1338828-95-7 ]
YieldReaction ConditionsOperation in experiment
83% With triethylamine; at 60℃; for 4h;Inert atmosphere; 2-Carboxyethyl acrylate (28.826 g, 0.2 mol), glycerol diglycidyl ether (20.433 g, 0.1 mol) and triethylamine (2 wt % based on glycerol diglycidyl ether) were sequentially added to a 4-bulb glass flask reactor equipped with a reflux condenser, a nitrogen inlet, a stirrer and a heater. After raising temperature to 60 C., reaction was carried out for 4 hours without using a polymerization inhibitor. Then, after cooling to room temperature and transferring to a reparatory funnel, 5% HCl aqueous solution was added to neutralize the remaining catalyst and the salt was removed. Then, after washing 2 to 3 times with distilled water, a Michael acceptor having hydroxyl groups was obtained at 50 C. under reduced pressure as transparent liquid. The Michael acceptor was separated and purified to obtain a main product with the byproduct removed.prep-LC (yield): 83%. IR (KBr, cm-1): 3421 (-OH), 2919 (aliphatic C-H), 1727 (C═O), 1635 & 1618 (C═C), 1186 & 1122 (C-O-C), 984 (═CH2 twisting vibration). 1H-NMR (CDCl3, 300 MHz), δ (ppm): 5.80-6.33 (m, 3H, -CH═CH2), 4.13 & 4.31-4.41 (m, 5H, -CH2CHOHCH2OOCCH2CH2-), 3.98 (m, 1H, -CH2CHOHCH2-), 3.55 & 3.70 (m, 4H, -CH2OCH2-), 2.61-2.72 (m, 2H, -CH2COO-). 13C-NMR (CDCl3, 75 MHz), δ (ppm): 173.63 (-CH2COO-), 165.99 (CH2═CHCOO-), 131.20 (CH2═CH-), 127.97 (CH2═CH-), 65.14-73.05 (-COOCH2CHOHCH2OCH2CHOH-), 59.83 (CH2=CHCOOCH2-), 33.18 (CH2═CHCOOCH2CH2-).
  • 32
  • [ 24615-84-7 ]
  • [ 142627-91-6 ]
  • C18H24O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With methanesulfonic acid; 2,6-di-tert-butyl-4-methyl-phenol; In toluene; at 80 - 110℃; for 2h;Dean-Stark; Inert atmosphere; In a three-port reactor equipped with a Dean-Stark Tube cooler and thermometer, in a nitrogen stream,Adding 10.00 g of brown crystal containing the intermediate product 12 synthesized in the above step 12,Toluene 100g, 2,6-di(tributyl)p-cresol 0.105g (0.476mmol),Stir the whole. Heat the solution to 80 C,20.56 g (0.1427 mol) of <strong>[24615-84-7]2-carboxyethyl acrylate</strong> and 1.37 g (14.3 mmol) of methanesulfonic acid were added under reflux conditions (110 C).The dehydration reaction was carried out for 2 hours while removing the generated water.Next, the reaction solution was cooled to 30 C.500 g of distilled water was added, and the whole was stirred and allowed to stand. The organic layer was separated, and 500 g of 5% brine was added to the obtained organic layer, and liquid-liquid extraction was carried out. The organic layer was separated, dried over anhydrous sodium sulfate and filtered. After concentration by a rotary evaporator, it was refined by a silica gel column chromatography (toluene: ethyl acetate = 8:1).In a total of 7.93 g of the intermediate product 13 as a white solid (yield: 40 mol%).
7.93 g With methanesulfonic acid; 2,6-di-tert-butyl-4-methyl-phenol; In toluene; at 80 - 110℃; for 2h;Dean-Stark; Into a three-necked reactor equipped with a condenser equipped with a Dean-Stark tube and a thermometer, 10.00 g of brown crystals containing the intermediate K synthesized in the above step 1, 100 g of toluene, 100 g of 2,6-di-t 0.105 g (0.476 mmol) of butyl-p-cresol was added, and the whole of the mixture was stirred. The solution was heated to 80 C., 20.56 g (0.1427 mol) of <strong>[24615-84-7]2-carboxyethyl acrylate</strong> and 1.37 g (14.3 mmol) of methanesulfonic acid were added, and the produced water was removed under reflux condition (110 C.) Dehydration reaction was carried out for 2 hours. Subsequently, the reaction solution was cooled to 30 C., 500 g of distilled water was added, and the whole of the mixture was stirred and then allowed to stand. The organic layer was separated, 500 g of 5% saline was added to the obtained organic layer, and the layers were separated. The organic layer was separated, dried over anhydrous sodium sulfate, and sodium sulfate was filtered off. After concentrating with a rotary evaporator, purification by silica gel column chromatography (toluene: ethyl acetate = 8: 1) gave 7.93 g of intermediate L as a white solid in total in steps 1 and 2 (yield : 40 mol%).
7.93 g With methanesulfonic acid; 2,6-di-tert-butyl-4-methyl-phenol; In toluene; at 110℃; for 2h;Inert atmosphere; Dean-Stark; Into a three-necked reactor equipped with a condenser equipped with a Dean-Stark tube and a thermometer, 10.00 g of brown crystals containing the intermediate K synthesized in the above step 1, 100 g of toluene, 10 g of 2,6-di-t 0.105 g (0.476 mmol) of butyl-p-cresol was added and the whole mixture was stirred. The solution was heated to 80 C., 20.56 g (0. 1427 mol) of <strong>[24615-84-7]2-carboxyethyl acrylate</strong> and 1.37 g (14.3 mmol) of methanesulfonic acid were added, and the generated water was removed under reflux condition (110 C.) Dehydration reaction was carried out for 2 hours. Subsequently, the reaction solution was cooled to 30 C., 500 g of distilled water was added, and the whole of the mixture was stirred and then allowed to stand. The organic layer was separated, 500 g of 5% saline was added to the obtained organic layer, and the layers were separated. The organic layer was separated, dried over anhydrous sodium sulfate, and sodium sulfate was filtered off. After concentrating with a rotary evaporator, purification by silica gel column chromatography (toluene: ethyl acetate = 8: 1) gave 7.93 g of intermediate L as a white solid in total in steps 1 and 2 ( Yield: 40 mol%).
  • 33
  • [ 79-10-7 ]
  • [ 24615-84-7 ]
  • C12H16O8 [ No CAS ]
  • [ 107825-26-3 ]
YieldReaction ConditionsOperation in experiment
With titanium(IV) isopropylate; 4-methoxy-phenol; hydroquinone; copper(l) chloride; at 140 - 148℃; for 24h; In a 500 ml four-neck reaction flask, with electric stirring, a thermometer, and a condenser, 360 g of acrylic acid, 3.6 g of titanium tetraisopropoxide, 0.29 g of p-methoxyphenol, 0.22 g of hydroquinone, and 3.6 g of chlorination were sequentially added. Cuprous, at 140-148 C, after 24 hours of reaction, the temperature is lowered, and the reaction product is obtained by filtration.High performance liquid chromatography analysis, product composition: acrylic acid 27.2%, acrylic acid dimer (β-carboxyethyl acrylate) 39.3%, acrylic acid trimer 20.6%, acrylic acid tetramer 8.5%, acrylic acid pentamer 3.6% , hexamethylene acrylate 0.8%.The obtained product was purified by distillation under an oil pressure diffusion pump at a pressure of 22 to 25 Pa at 101 to 103 C.The product obtained was 340.5 g (yield: 94.6%), and the product composition was 28.3% of acrylic acid, 40.5% of dimer of acrylic acid (β-carboxyethyl acrylate), 21.6% of trimer of acrylic acid, 9.1% of tetramer of acrylic acid, acrylic acid. Pentamer 0.5%
  • 34
  • [ 6066-82-6 ]
  • [ 24615-84-7 ]
  • C10H11NO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 20h; Take 11.5g (0.1mol) N-hydroxysuccinimide dissolved in 80mL dichloromethane,A solution of 15.8 g (0.11 mmol) of acryloyloxypropionic acid and 22.67 g (0.11 mol) of DCC in methylene chloride was added dropwise, and the reaction was carried out at room temperature for 20 hours.The reaction solution was washed sequentially with saturated NaHCO3 and deionized water, and the organic phase was dried over anhydrous magnesium sulfate;With ethyl acetate and n-hexane as eluents,After purification by column chromatography, 18.6 g of colorless viscous liquid was obtained, which was active monomer B, with a yield of 77%.
  • 35
  • [ 24615-84-7 ]
  • [ 2530-85-0 ]
  • C25H32O14Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; at 20℃; for 3h;Darkness; Inert atmosphere; 10 gram of MEMO is dissolved in 50 ml water free ethyl acetate. The aciyloyloxy-propanoic acid is added in accordance with predefined molar amounts. The reaction mixture is stirred 3 hours in a dark environment under nitrogen atmosphere at room temperature. Thereafter, the ethyl acetate solvent and formed methanol are removed by evaporation (rotavapor).
Same Skeleton Products
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